EP4153650B1 - Verfahren zur wiederverwertung eines polyurethanmaterials - Google Patents

Verfahren zur wiederverwertung eines polyurethanmaterials

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Publication number
EP4153650B1
EP4153650B1 EP21808452.3A EP21808452A EP4153650B1 EP 4153650 B1 EP4153650 B1 EP 4153650B1 EP 21808452 A EP21808452 A EP 21808452A EP 4153650 B1 EP4153650 B1 EP 4153650B1
Authority
EP
European Patent Office
Prior art keywords
compound
polyurethane material
process according
polyol
isocyanate
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
EP21808452.3A
Other languages
English (en)
French (fr)
Other versions
EP4153650A1 (de
EP4153650A4 (de
Inventor
Amit Sharma
Daniel Heberer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Huntsman International LLC
Original Assignee
Huntsman International LLC
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Filing date
Publication date
Application filed by Huntsman International LLC filed Critical Huntsman International LLC
Publication of EP4153650A1 publication Critical patent/EP4153650A1/de
Publication of EP4153650A4 publication Critical patent/EP4153650A4/de
Application granted granted Critical
Publication of EP4153650B1 publication Critical patent/EP4153650B1/de
Active legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J11/00—Recovery or working-up of waste materials
    • C08J11/04—Recovery or working-up of waste materials of polymers
    • C08J11/10—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation
    • C08J11/18—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material
    • C08J11/22—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material by treatment with organic oxygen-containing compounds
    • C08J11/26—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material by treatment with organic oxygen-containing compounds containing carboxylic acid groups, their anhydrides or esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4825—Polyethers containing two hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
    • C08G18/1816—Catalysts containing secondary or tertiary amines or salts thereof having carbocyclic groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
    • C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J11/00—Recovery or working-up of waste materials
    • C08J11/04—Recovery or working-up of waste materials of polymers
    • C08J11/10—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation
    • C08J11/14—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with steam or water
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J11/00—Recovery or working-up of waste materials
    • C08J11/04—Recovery or working-up of waste materials of polymers
    • C08J11/10—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation
    • C08J11/18—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material
    • C08J11/22—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material by treatment with organic oxygen-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J11/00—Recovery or working-up of waste materials
    • C08J11/04—Recovery or working-up of waste materials of polymers
    • C08J11/10—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation
    • C08J11/18—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material
    • C08J11/28—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material by treatment with organic compounds containing nitrogen, sulfur or phosphorus
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2110/00—Foam properties
    • C08G2110/0008—Foam properties flexible
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2110/00—Foam properties
    • C08G2110/0083—Foam properties prepared using water as the sole blowing agent
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
    • C08J2375/04—Polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
    • C08J2375/04—Polyurethanes
    • C08J2375/08—Polyurethanes from polyethers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/582—Recycling of unreacted starting or intermediate materials
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
    • Y02W30/00—Technologies for solid waste management
    • Y02W30/50—Reuse, recycling or recovery technologies
    • Y02W30/62—Plastics recycling; Rubber recycling

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Sustainable Development (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)

Claims (19)

  1. Verfahren zum Recyceln eines Polyurethanmaterials, wobei das Polyurethanmaterial einen Teil umfasst, der in der Lage ist, sich einer Zersetzung durch eine Acidolyse zu unterziehen, das Verfahren umfassend:
    Inberührungbringen des Polyurethanmaterials mit einer Säurelösung und Ermöglichen, dass sich mindestens ein Anteil des Polyurethanmaterials zu einer zurückgewonnenen Rohmaterialzusammensetzung zersetzt, umfassend: (i) eine Abbauverbindung; und
    Einführen eines acetoacetylierten Polyols in die zurückgewonnene Rohmaterialzusammensetzung und Umsetzen des acetoacetylierten Polyols und einer Komponente (i), um eine Polyolverbindung auszubilden (zz).
  2. Verfahren nach Anspruch 1, wobei die zurückgewonnene Rohmaterialzusammensetzung ferner umfasst: (ii) eine hydroxyfunktionell terminierte Urethanverbindung, (iii) eine hydroxyhaltige Verbindung, die sich von einer Komponente (ii) unterscheidet, (iv) eine Hilfsverbindung oder Kombinationen davon.
  3. Verfahren nach Anspruch 1, wobei die Säurelösung eine Säureverbindung, Wasser und (yy) eine Polyolverbindung umfasst.
  4. Verfahren nach Anspruch 3, wobei die Säureverbindung einen pH-Wert ≤ 2 aufweist.
  5. Verfahren nach Anspruch 3, wobei die Säureverbindung mit einer Komponente (yy) mischbar ist.
  6. Verfahren nach Anspruch 3, wobei die zurückgewonnene Rohmaterialzusammensetzung mindestens einen Anteil der Säurelösung enthält, die das Polyurethanmaterial berührt, und das Verfahren ferner ein Extrahieren von Wasser aus der Rohmaterialzusammensetzung umfasst.
  7. Verfahren nach Anspruch 1, wobei die Komponente (i) eine Aldehydverbindung, eine Ketonverbindung oder Kombinationen davon ist.
  8. Verfahren nach Anspruch 1, wobei das Verfahren ferner ein Verwenden einer oder mehrerer der Komponenten (i)-(iv) und (zz) als ein Rohmaterial bei der Herstellung eines anderen Materials umfasst.
  9. Verfahren nach Anspruch 8, wobei das Verfahren ferner das Extrahieren einer oder mehrerer der Komponenten (i)-(iv) und (zz) aus der zurückgewonnenen Rohmaterialzusammensetzung umfasst, bevor diese als das Rohmaterial verwendet wird.
  10. Verfahren nach Anspruch 1, wobei das Verfahren ein Eintauchen mindestens eines Anteils des Polyurethanmaterials in die Säurelösung umfasst.
  11. Verfahren nach Anspruch 1, wobei das gesamte Polyurethanmaterial in die Säurelösung eingetaucht wird.
  12. Verfahren nach Anspruch 1, wobei das Verfahren ferner ein Rühren des Polyurethanmaterials während der Acidolyse umfasst, um die Zersetzung des Polyurethanmaterials zu fördern.
  13. Verfahren nach Anspruch 1, wobei das Verfahren ein Anwenden von Wärme auf das Polyurethanmaterial während der Acidolyse umfasst, um die Zersetzung des Polyurethanmaterials zu fördern.
  14. Verfahren nach Anspruch 1, wobei das Verfahren ein Durchführen der Acidolyse unter Vakuum umfasst, um die Zersetzung des Polyurethanmaterials zu fördern.
  15. Verfahren nach Anspruch 1, wobei das Polyurethanmaterial Acetalteile in seinem polymeren Rückgrat umfasst.
  16. Verfahren nach Anspruch 1, wobei das Polyurethanmaterial das Reaktionsprodukt einer Isocyanatverbindung und einer isocyanatreaktiven Verbindung ist, wobei die isocyanatreaktive Verbindung eine Polyolverbindung umfasst, umfassend einen Acetalteil, einen Orthoesterteil oder Kombinationen davon.
  17. Verfahren nach Anspruch 1, wobei das Polyurethanmaterial das Reaktionsprodukt einer Isocyanatverbindung und einer isocyanatreaktiven Verbindung ist, wobei die isocyanatreaktive Verbindung das Reaktionsprodukt ist von: (a) einer Polyolverbindung und (b) einer Divinyletherverbindung, wobei eine Komponente (a) in einem molaren Überschuss zu einer Komponente (b) ist.
  18. Verfahren nach Anspruch 1, wobei das acetoacetylierte Polyol das Reaktionsprodukt eines acetoacetylfunktionellen Monomers mit einer Polyetherpolyolverbindung ist.
  19. Verfahren nach Anspruch 1, wobei das acetoacetylierte Polyol bis zu 40 % acetoacetylfunktionelle Gruppen umfasst, die auf verfügbaren Hydroxylgruppen in dem acetoacetylierten Polyol basieren.
EP21808452.3A 2020-05-19 2021-05-12 Verfahren zur wiederverwertung eines polyurethanmaterials Active EP4153650B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US202063027134P 2020-05-19 2020-05-19
PCT/US2021/031900 WO2021236385A1 (en) 2020-05-19 2021-05-12 A process for recycling a polyurethane material

Publications (3)

Publication Number Publication Date
EP4153650A1 EP4153650A1 (de) 2023-03-29
EP4153650A4 EP4153650A4 (de) 2025-03-12
EP4153650B1 true EP4153650B1 (de) 2026-04-01

Family

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Family Applications (1)

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EP21808452.3A Active EP4153650B1 (de) 2020-05-19 2021-05-12 Verfahren zur wiederverwertung eines polyurethanmaterials

Country Status (6)

Country Link
US (1) US12503567B2 (de)
EP (1) EP4153650B1 (de)
CN (1) CN115702181B (de)
CA (1) CA3183168A1 (de)
MX (1) MX2022014487A (de)
WO (1) WO2021236385A1 (de)

Families Citing this family (5)

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FR3135720B1 (fr) * 2022-05-23 2025-10-17 Faurecia Sieges Dautomobile Recyclage de polyol produit à partir de mousse en polyuréthane moulée
WO2024133897A1 (en) 2022-12-23 2024-06-27 Basf Se Process for preparation of polyacetalpolyols and their application in pu systems
TWI866606B (zh) * 2023-11-14 2024-12-11 上緯創新育成股份有限公司 自聚氨酯廢料回收多元醇的方法
WO2025111047A1 (en) * 2023-11-20 2025-05-30 Dow Global Technologies Llc Acidolysis of polyurethane to polyol products using vapor phase
WO2025262292A1 (en) 2024-06-21 2025-12-26 Basf Se Process for obtaining polyacetalpolyols from water solution of formaldehyde and alcohols

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Also Published As

Publication number Publication date
EP4153650A1 (de) 2023-03-29
US20230183444A1 (en) 2023-06-15
WO2021236385A1 (en) 2021-11-25
EP4153650A4 (de) 2025-03-12
CA3183168A1 (en) 2021-11-25
MX2022014487A (es) 2022-12-13
US12503567B2 (en) 2025-12-23
CN115702181B (zh) 2025-08-19
CN115702181A (zh) 2023-02-14

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